Chicago
Chicago is the ultimate American city, welcoming visitors to a one-of-a-kind experience. Stroll the downtown streets of one of the most walkable cities in the U.S. and explore block after block of outstanding architecture that makes up Chicago’s breathtaking skyline.
At a glance
- On the shores of Lake Michigan
- Stunning architecture
- Award winning restaurants, theatre and music
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-6 hours
Time Difference -
English
Language Speaking -
9 hours
Flight Time -
$USD
Currency -
Chicago O'Hare International (ORD)
Nearest Airport
Special Offers
Take a look at our current special offers
Canyon Spirit Early Booking Bonus
Save up to £275 off per person
Save up to £275 off per person on selected 2027 Canyon Spirit departures. Applicable for selected 2027 two or three-day Rail Only journeys on Canyon Spirit’s USA routes. Book by 30th June 2026.
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Cruise America Motorhome Offer
Save up to 10% on nightly rental rates
Book a motorhome with Cruise America and save up to 10% on nightly rentals. Book by 16th May 2026.
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Cruise America Motorhome Mileage Package Discount
Receive a 50% discount on prebooked mileage packages
Book a motorhome with Cruise America and receive a 50% discount on prebooked mileage packages. Book by 16th May 2026.
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Cruise America Motorhome 2026 Offer
Unlimited mileage package for free
Book a motorhome rental with Cruise America and receive the Unlimited Mileage package for free. Book by 31st May 2026.
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Celebrity Cruises Spring Sale
Receive at least 30% off 1st and 2nd Guests on selected cruises
The first two guests sharing a stateroom receive at least 30% off per person on selected cruises. Book by 3rd May 2026.
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Best time to visit Chicago
The best time to visit Chicago is during the spring (April to June) and autumn (September to early November). These seasons offer mild and pleasant weather, fewer tourists, and a variety of events and activities to enjoy.
Spring (April to June) is a fantastic time to explore the city. The weather is mild, with temperatures ranging from 7°C to 24°C, making it perfect for outdoor activities. During this period, you can enjoy events like the Chicago Flower & Garden Show and the St. Patrick's Day Parade. The city's parks and gardens come to life with blooming flowers, providing a beautiful backdrop for sightseeing and leisurely strolls.
Autumn (September to early November) is another excellent time to visit Chicago. The temperatures are comfortable, ranging between 10°C and 21°C, making it ideal for exploring the city on foot. Fall also brings a variety of events, such as the Chicago International Film Festival, Oktoberfest, and Halloween celebrations. The city's parks and streets are adorned with stunning fall foliage, perfect for scenic walks and photography.
Both spring and autumn provide an excellent balance of enjoyable weather and engaging activities without the extreme temperatures of summer and winter, making them the best times to visit Chicago.
Average temperatures by month
- JAN -6°
- FEB -4°
- MAR 3°
- APR 10°
- MAY 15°
- JUN 21°
- JUL 23°
- AUG 22°
- SEP 18°
- OCT 12°
- NOV 5°
- DEC -3°
Contact our travel experts to start planning your holiday to Chicago
Contact usRecommended Chicago holidays
Explore a collection of our handpicked holidays to Chicago below
Architecture, Music & The French Quarter
This holiday showcases the USA’s rich musical heritage of bluegrass, country, rock 'n' roll, rhythm 'n' blues and soul.
10 Nights From
£1,569
ppOverview
This holiday showcases the USA’s rich musical heritage of bluegrass, country, rock 'n' roll, rhythm 'n' blues and soul.
What’s included?
- International flights from the UK in economy class
- Accommodation for 9 nights
- Amtrak from Chicago to Memphis and Memphis to New Orleans in Coach class
Route 66 – Classic Americana
Passing through eight states and covering three time zones, Route 66 is the classic self-drive trip that gives great insight into a journey well-travelled.
15 Nights From
£1,969
ppOverview
Passing through eight states and covering three time zones, Route 66 is the classic self-drive trip that gives great insight into a journey well-travelled.
What’s included?
- International flights from the UK based on economy class
- Accommodation for 15 nights
- 14 days intermediate car hire with fully inclusive insurance, unlimited mileage and taxes
America's Music Cities
Travel from the windy city of Chicago, along famous Route 66 to New Orleans the home of jazz music. Other highlights include the music cities of Memphis, Nashville, and Muscle Shoals.
15 Nights From
£2,219
ppOverview
Travel from the windy city of Chicago, along famous Route 66 to New Orleans the home of jazz music. Other highlights include the music cities of Memphis, Nashville, and Muscle Shoals.
What’s included?
- International flights from the UK based on economy class
- Accommodation for 15 nights
- Graceland Elvis Experience Tour including Airplanes
- 10 days intermediate car hire with insurance coverage, unlimited mileage, and taxes
Great Lakes Explorer
Centred around some of the world’s most amazing natural wonders, this trip will take you to three of the Great Lakes and Great Lake states
13 Nights From
£2,264
ppOverview
Centred around some of the world’s most amazing natural wonders, this trip will take you to three of the Great Lakes and Great Lake states
What’s included?
- International flights from the UK based on economy class
- Accommodation for 13 nights
- 12 days intermediate car hire with insurance coverage, unlimited mileage and taxes
Discover Route 66 by Rail
Ride the rails from Chicago to Los Angeles and get your kicks on Route 66.
15 Nights From
£2,509
ppOverview
Ride the rails from Chicago to Los Angeles and get your kicks on Route 66.
What’s included?
- International flights departing from the UK based in economy class
- Accommodation for 15 nights
- Amtrak train from Chicago to St Louis in Coach class
- Amtrak overnight train from St Louis to Albuquerque in Coach class
- Amtrak train from Albuquerque to Flagstaff in Coach class
- Return Amtrak transfers from Flagstaff to Williams
- Amtrak overnight train from Williams to Los Angeles in Coach class
- One day Chicago Hop on/off Bus tour
- 90-minute St Louis Narrated Trolley Tour
- Round trip Grand Canyon Railway from Williams to the Grand Canyon
- One day Los Angeles Hop-on Hop-off Bus tour
The Ultimate Michigan & Great Lakes Explorer
This trip will take you to all five of the Great Lakes including three Great Lake States plus the Canadian Province of Ontario. From pristine waters to remarkable national parks, there is so much to explore and discover on this amazing holiday.
16 Nights From
£2,943
ppOverview
This trip will take you to all five of the Great Lakes including three Great Lake States plus the Canadian Province of Ontario. From pristine waters to remarkable national parks, there is so much to explore and discover on this amazing holiday.
What’s included?
- International flights from the UK based on economy class
- Accommodation for 16 nights
- 15 days compact car hire with fully inclusive insurance, unlimited mileage and taxes
Iconic Route 66 by Motorhome with Campgrounds
Get your kicks out of Route 66 on this motorhome holiday soaking up true Americana, beautiful national parks and historic, buzzing and authentic cities and towns.
19 Nights From
£3,879
ppOverview
Get your kicks out of Route 66 on this motorhome holiday soaking up true Americana, beautiful national parks and historic, buzzing and authentic cities and towns.
What’s included?
- International flights from the UK based on economy class
- Accommodation for 2 nights
- 18 days Cruise America motorhome hire
- Campgrounds for 17 nights
- Unlimited Mileage package
- Personal & vehicle kits
- A digital travel guide-book companion taking you to those hidden gems so easily missed without an expert’s advice
Journey Across the USA by Rail
Perfect for rail enthusiasts and for non-drivers this epic coast to coast rail tour includes the iconic and much-loved cities of New York, Washington DC, Chicago, Los Angeles and San Francisco and the awe-inspiring wonder of the Grand Canyon.
18 Nights From
£3,919
ppOverview
Perfect for rail enthusiasts and for non-drivers this epic coast to coast rail tour includes the iconic and much-loved cities of New York, Washington DC, Chicago, Los Angeles and San Francisco and the awe-inspiring wonder of the Grand Canyon.
What’s included?
- International flights departing from the UK in economy class.
- Accommodation for 18 nights
- Amtrak train from New York to Washington DC in Coach Class
- Amtrak overnight Floridian from Washington DC to Chicago staying in a roomette
- Amtrak overnight Southwest Chief from Chicago to Flagstaff staying in a roomette
- Amtrak overnight Southwest Chief from Flagstaff to Los Angeles staying in a roomette
- Amtrak Coast Starlight from Los Angeles to Emeryville in Coach Class
- One day hop on/off bus tour of New York
- One day hop on/off bus tour of Washington DC
- One day hop on/off bus tour of Chicago
- Full day Grand Canyon tour from Flagstaff
- One day hop on/off bus tour of Los Angeles
- Two day hop on/off bus tour of San Francisco including Alcatraz
The Canadian Rockies & Glacier National Park by Rail
Experience the majestic scenery of Glacier National Park and the Canadian Rockies on this epic rail journey that includes stays in the world-class cities of Chicago, Seattle and Vancouver.
16 Nights From
£5,401
ppOverview
Experience the majestic scenery of Glacier National Park and the Canadian Rockies on this epic rail journey that includes stays in the world-class cities of Chicago, Seattle and Vancouver.
What’s included?
- nternational flights departing from London in economy class
- Accommodation for 13 nights
- Amtrak overnight Empire Builder from Chicago to Glacier National Park staying in a roomette
- Full day Glacier National Park tour by open-top Red Bus
- Amtrak overnight Empire Builder from Glacier National Park to Seattle staying in a roomette
- Amtrak Cascade service from Seattle to Vancouver in coach class
- VIA Rail The Canadian overnight train from Vancouver to Jasper staying in berth accommodation
- Icefield Parkway tour including Ice Explorer, Glacier Skywalk and lunch from Jasper to Lake Louise
- Half day sightseeing tour of Banff
- Scheduled transfer from Lake Louise to Banff
- Scheduled transfer from Banff to Calgary airport
Cruising The Great Lakes with Victory Cruise Lines
Cruise all five Great Lakes on Victory Cruise lines, a small ship style cruise with premium amenities, tasty cuisine and unlimited adventures.
14 Nights From
£5,753
ppOverview
Cruise all five Great Lakes on Victory Cruise lines, a small ship style cruise with premium amenities, tasty cuisine and unlimited adventures.
What’s included?
- International flights from the UK in economy class
- Accommodation for 4 nights
- 1 night pre-cruise accommodation in Toronto
- 9 nights on board Victory Cruise Lines in an xxx cabin
- All meals, non-alcoholic and selected alcoholic drinks
- One standard shore excursion in selected ports of call
Explore Chicago
Discover Chicago's top attractions with our interactive map
City / Destination
Point of interest
Snapshot of Chicago
Discover the magic of Chicago, where striking architecture meets a rich cultural scene and exceptional cuisine. From its iconic skyline and lakeside strolls to immersive museums and legendary deep-dish pizza, Chicago offers a unique adventure for every traveller.
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